Ammonia → 1H-Benzimidazol-6-amine, 5-chloro-1-(1-methylethyl)-2-(4-methyl-1-piperazinyl)-

HRID 1654484Notes

Reaction equation

[Cl:1][C:2]1[C:20]([N+:21]([O-])=O)=[CH:19][C:5]2[N:6]([CH:16]([CH3:18])[CH3:17])[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1.N>Cl.[Zn]>[NH2:21][C:20]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)[N:6]([CH:16]([CH3:18])[CH3:17])[C:5]=2[CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5-Chloro-1-isopropyl-2-(4-methyl-1-piperazinyl)-6-nitrobenzimidazole (1.2 g) was dissolved in 2.5N hydrochloric acid (20 ml) and thereto was added zinc powder (1.5 g) in portions and the mixture was stirred at 80° C. for 4 hours. The reaction mixture was made basic with an aqueous ammonia and extracted with chloroform. The chloroform layer was washed with water and dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. The residue was recrystallized from acetonitrile to give 6-amino-5-chloro-1-isopropyl-2-(4-methyl-1-piperazinyl)benzimidazole (0.6 g) as colorless crystal.

Workup

extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record: ord-9dfa155afd594b38a1759cd62cfa4652
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05407936

Reaction notes

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